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    Viewed 8 times in the last 48 hours
    • 5 bedrooms
    • 3 bathrooms
    • 2 HF BA
    • Sleeps 9
    Favorite
      Viewed 7 times in the last 48 hours
      • 6 bedrooms
      • 5 bathrooms
      • 1 HF BA
      • Sleeps 13
      Favorite
        Viewed 8 times in the last 48 hours
        • 10 bedrooms
        • 9 bathrooms
        • 1 HF BA
        • Sleeps 17
        Favorite
          Viewed 11 times in the last 48 hours
          • 7 bedrooms
          • 7 bathrooms
          • 1 HF BA
          • Sleeps 14
          Favorite
            Viewed 10 times in the last 48 hours
            • 7 bedrooms
            • 9 bathrooms
            • 1 HF BA
            • Sleeps 14
            • 1 - 5 of 5

            Pittsfield: Vacation Rental Estates (5)

             

            Recent Pittsfield Reviews

            BEAUTIFUL PROPERTY and GREAT LOCATION!

            5 of 5
            My friends and I had a great holiday on this property. The house was beautifully renovated so that the character of property still shined through and at the same time provided all the modern conveniences one could desire! It was also well appointed with anything we could ever need. Just a couple blocks to all the restaurants and shops made the location ideal. We will definitely come back when it is warmer out so that we can take advantage of the pool :)
            • Submitted: Feb 28, 2017
            • Stayed: Feb 2017

            Luxurious Rockefeller-like New England mansion

            5 of 5
            I travel extensively throughout the world for my work and have stayed at many of the worlds great hotels. Quite frankly, I was not expecting but was pleasantly surprised to discover a world class property in the tiny town of Lenox. The Winthrop Estate is a perfect marriage of an historical Rockefeller-like New England mansion of the 1920s and a Four Seasons hotel of today. This is how we’d describe our stay at Winthrop Estate. The experience was nothing short of going back a hundred years to the days when The Berkshires were a pastoral retreat for the great Industrialists and statesmen of the day while enjoying the luxury of the current era. The Winthrop Estate is neatly tucked away, thus we experienced as little or as much of civilization as we desired. In the morning we took a walk to the center of Lenox (a sleepy but adorable typical New England town), which is just a five minutes away. We stopped at a bagel shop, then got coffee at a French patisserie, and then just walked and enjoyed the tranquility and simple beauty of this historic area. The Winthrop Estate was a perfect place to decompress from the busyness of everyday life. We really enjoyed our stay and highly recommend this treasure to everyone.
            • Submitted: Jun 14, 2015
            • Stayed: Nov 2014